Generally speaking, I'd rather recommend strobes over hot lights, but unless you can scrape together a little more money, you're going to have a hard time getting into decent equipment for only 300 clams. Life will be a lot easier for you if you can also afford a light meter.

Strobe-wise, for 300 I'd say get an Alien bees B400, then use the rest of your cash to get a light stand off ebay (I snagged a decent 12' stand for 16 bux a few months ago, takes patience). The B400 doesn't have a lot of power, but there's still a lot you can do with it, as I often use mine as a main light and I can get f11 through a softbox. The AB lights are nice in that you can upgrade them to a higher power model later on when you've got more cash together.

The AB lights are just about as light and portable as a monolight is going to get. For another $13 they'll sell you a cool little bag to carry the light in.

There are some good deals on used equipment on ebay, but even then I'm not sure how far $300 will take you.

I second ebay though I differ on the brand. I may get the stink eye for this, but I think with Novatrons get you the most bang for your buck. For $212+ship I was able to snag a Novatron 440 system, with a regular head, head w/1 stop reduction, one barbulb, and a non functioning head along with four stands, barn doors, and snoot. It wasn't in the greatest shape, but after some steele wool and metal polish it looks ok an works like a charm. Some might raise objections about the novatrons, but the only accessory I haven't been able to find for them are beauty dishes. Several softbox mfrs make speed rings for them. If you do end up getting an older system, make sure you check the trigger voltage before hooking you're camera up to it. I have a Bowens monolight (they're cheap too) that has a 250v trigger, yikes!

For $300, ease of portability, small, lightweight....
Maybe get 2 Vivitar 283/285 units, a couple of sync slaves, light stands, umbrellas. If you want a softbox, there are several options too, for use w/ Vivitars. And, um, a case of AA batteries or some good rechargables.
Vivitars can even be great once you upgrade. I ocassionally use them to pop gels as accents on backdrops or products.

I would suggest getting the lights new, and check out eBay for the stands and stuff.

I've used a setup like this before for portrait shoots in parks and such.

Also, someone mentioned the Alien Bee lights. I have a friend that uses those and he loves them. Very small, portable, ilghtweight, dependable.

I would second the AB 400 suggestion. I am really happy with my 1600 and my 800. My first purchase was a jtl cheapy 110 light. It did teach me some things once I got a meter. Like the adjustment knob on the back was apparently just there for looks as it doesn't seem to work. Now it serves out its remaining sentence as a hairlight. My bees of course meter up and down just fine.

I have been told several times that the best way to start is with one light and to actually learn how the light works. Then add something reflective and you are on your way.

These are hot lights. I fyou are interested in hot lights you may want to just go the Home Depot route and save your money until you decide if you would like to stick with hot lights or use strobes.

If you decide to stick with hot lights you can always save money and get nice ones. If you decide you would prefer to go with strobes you won't be out a lot of money on hot lights you don't want to use.

I know what it is like to have some money burning a hole in the ole pocket begging to be spent on some photography equipment believe me. But save yourself some frustration and wait until you can afford something adequate before you spend too much.

hmmm.... just 300 bucks, huh? well, i think i'd buy an IR transmitter like a wein or something, and then i'd be watching the newspaper or hitting garage sales and/or swap meets looking for some old, used, strobes like vivitars and others, but only one's that have an optical trigger.